Trifluoroacetic acid → HCID 59398036, compound

HRID 2193216Notes

Reaction equation

HRID 2193216 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10](/[CH:19]=[CH:20]/[C:21]([NH2:23])=[O:22])=[CH:9][C:8]1=[O:24].FC(F)(F)C(O)=O>>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11]([C:10](/[CH:19]=[CH:20]/[C:21]([NH2:23])=[O:22])=[CH:9][C:8](=[O:24])[N:7]2[CH2:6][CH:2]=[O:1])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398025HCID 59398025, compound

Product 1

HCID 59398036HCID 59398036, compoundYield 56.5%

Procedure

To 0.20 g of (2E)-3-(1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)-acrylamide, 5 mL of 80% aqueous trifluoroacetic acid solution was added, and stirred at room temperature for 4 hours, thereafter allowed to stand at the same temperature overnight. After the solvent was removed under reduced pressure, water was added and adjusted to pH 7.8 with 1.0 mol/L aqueous sodium hydroxide solution. The resulting solid was filtered to give 98 mg of (2E)-3-(7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinolin-4-yl)acrylamide as a light brown solid.

Workup

  1. customto stand at the same temperature overnight
  2. customAfter the solvent was removed under reduced pressure, water
  3. additionwas added
  4. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-505d3655d9da484a81bfe21e8500a980
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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